Hydrochloric Acid → HCID 69669367, compound

HRID 929999Notes

Reaction equation

HRID 929999 reaction equation
[C:1]1([C:14]2[CH:15]=[C:16](Br)[CH:17]=[C:18]([C:20]3[C:32]4[NH:31][C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:24]=4[CH:23]=[CH:22][CH:21]=3)[CH:19]=2)[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[B:39](OC)([O:42]C)[O:40]C.Cl>O1CCCC1>[C:1]1([C:14]2[CH:15]=[C:16]([B:39]([OH:42])[OH:40])[CH:17]=[C:18]([C:20]3[C:32]4[NH:31][C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[C:24]=4[CH:23]=[CH:22][CH:21]=3)[CH:19]=2)[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 23089769HCID 23089769, compoundHCID 178418339Butyllithium

Product 1

HCID 69669367HCID 69669367, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an Ar atmosphere, 3,5-dicarbazolylbromobenzene (4.87 g, 0.01 mol) and 100 mL THF (tetrahydrofuran) were added into a 250 mL single-necked flask, then 9.4 mL n-BuLi (n-butyllithium) (1.6 M n-hexane solution) was added, stirred and reacted at −78° C. for 1.5 h. After this, trimethyl borate was added and reacted for 12 h, and then 20 mL hydrochloric acid solution was added, acidified for 0.5 h. After the reaction was completed, we carried out liquid separation, drying, and concentrating under reduced pressure, and obtained 3,5-dicarbazolylphenylboronic acid by column chromatography. The reaction process is as follows:

Workup

  1. customreacted at −78° C. for 1.5 h
  2. customreacted for 12 h
  3. customliquid separation
  4. customdrying
  5. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-e1131bb6cc6340f4a58e07cb57e9e637
Source dataset
uspto-grants-2016_03
Patent number
US09296738B2

Reaction notes

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